Tetrahydrofuran → HCID 54476053, compound

HRID 2293697Notes

Reaction equation

HRID 2293697 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1N.C[N+:8]([CH3:11])(C)C.C1C=C2C(C=C(C([S-])=S)C=C2)=CC=1.C([Li])CCC.[CH2:30]1[CH2:34][O:33][CH2:32][CH2:31]1>>[CH:30]1([CH:34]([C:2]2[S:1][C:5]([CH2:11][NH2:8])=[CH:4][CH:3]=2)[OH:33])[CH2:31][CH2:32]1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 51107Ammonium, tetramethyl-, 2-dithionaphthoateHCID 973732-AminothiopheneHCID 178418339Butyllithium

Product 1

HCID 54476053HCID 54476053, compound

Conditions

Temperature
0 °C

Procedure

Thienylamine of formula SS-1 (0.95 mL) is dissolved in dry THF under a nitrogen atmosphere and cooled to -78° C. n-Butyllithium (Aldrich, 1.6M in hexane, 13.4 mL) is added and the reaction turned a deep purple color. The reaction is allowed to warm to 0° C. for 10 min, then recooled to -78° C. for the addition of the aldehyde (0.82 mL). A thick slurry forms and stirring becomes difficult. The reaction is allowed to warm to 0° C., then quenched with ammonium chloride solution (10 mL). The reaction is extracted with EtOAc (200 mL) and washed with water (2×40 mL) and brine. The organic phase is dried over MgSO4, filtered and concentrated in vacuo. Chromatography over silica gel (300 g) eluting with 5% MeOH in CH2Cl2 gives the title product (356 mg) as a colorless oil.

Workup

  1. additionis added
  2. temperatureto warm to 0° C.
  3. customquenched with ammonium chloride solution (10 mL)
  4. extractionThe reaction is extracted with EtOAc (200 mL)
  5. washwashed with water (2×40 mL) and brine
  6. dry with materialThe organic phase is dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. washChromatography over silica gel (300 g) eluting with 5% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-bad55f8c126c4989bc3028debbc5cc35
Source dataset
uspto-grants-1997_11
Patent number
US05686486

Reaction notes

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